WO2005092897A2 - Cetoenols cycliques 2,4,6-phenylsubstitues - Google Patents

Cetoenols cycliques 2,4,6-phenylsubstitues Download PDF

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Publication number
WO2005092897A2
WO2005092897A2 PCT/EP2005/002605 EP2005002605W WO2005092897A2 WO 2005092897 A2 WO2005092897 A2 WO 2005092897A2 EP 2005002605 W EP2005002605 W EP 2005002605W WO 2005092897 A2 WO2005092897 A2 WO 2005092897A2
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Prior art keywords
alkyl
alkoxy
compounds
optionally
formula
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PCT/EP2005/002605
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German (de)
English (en)
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WO2005092897A3 (fr
Inventor
Thomas Bretschneider
Reiner Fischer
Oliver Gaertzen
Klaus Kunz
Stefan Lehr
Dieter Feucht
Peter Lösel
Olga Malsam
Guido Bojack
Christian Arnold
Thomas Auler
Martin Jeffrey Hills
Heinz Kehne
Chris Rosinger
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Bayer Cropscience Ag
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Priority to BRPI0507876A priority Critical patent/BRPI0507876B1/pt
Priority to AU2005225508A priority patent/AU2005225508A1/en
Priority to US10/594,251 priority patent/US7947704B2/en
Priority to KR1020067021888A priority patent/KR101137808B1/ko
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to EP05728341A priority patent/EP1732930B1/fr
Priority to AT05728341T priority patent/ATE556078T1/de
Priority to MXPA06010781A priority patent/MXPA06010781A/es
Priority to CA002561076A priority patent/CA2561076A1/fr
Priority to ES05728341T priority patent/ES2384175T3/es
Priority to JP2007504296A priority patent/JP5004788B2/ja
Publication of WO2005092897A2 publication Critical patent/WO2005092897A2/fr
Priority to UAA200611221A priority patent/UA85872C2/uk
Publication of WO2005092897A3 publication Critical patent/WO2005092897A3/fr
Priority to US13/087,696 priority patent/US20110195842A1/en
Priority to US13/087,879 priority patent/US20110213160A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/54—Spiro-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

Definitions

  • the present invention relates to new 2,4,6-phenyl-substituted cyclic ketoenols, several processes for their preparation and their use as pesticides and / or herbicides.
  • the invention also relates to new selective herbicidal combinations of active ingredients which contain 2,4,6-phenyl-substituted cyclic ketoenols on the one hand and at least one compound which improves crop compatibility on the other hand and which can be used with particularly good success for selective weed control in various crops of useful plants.
  • EP-A-0262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-aryl-pyrrolidin-2,4-diones), of which no herbicidal, insecticidal or acaricidal activity has been disclosed.
  • Unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives EP-A-355 599 and EP-A-415 211 and JP-A-12-053 670
  • substituted ones are known with herbicidal, insecticidal or acaricidal activity monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442077).
  • EP-A-442 073 and 1H-arylpyrrolidine-dione derivatives are also known , EP-A-613 884, EP-A-613 885, WO 94/01 997, WO 95/26954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02243, WO 97/36 868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03
  • 3-Aryl- ⁇ 3 - dihydrothiphen-one derivatives are also known (WO 95/26 345, 96/25 395, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05638, WO 98/25928, WO 99/16748, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/062244, WO 04/080962, DE-A-10326386).
  • Phenylpyrone derivatives substituted in the phenyl ring with herbicidal, acaricidal and insecticidal properties are described in EP-A-588 137, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97 / 16 436, WO 97/19 941, WO 97/36 868, WO 98/05638, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972 and WO 01/74770, WO 03/062244 , WO 04/080962, DE-A-10326386.
  • 5-phenyl-1,3-thiazine derivatives substituted in the phenyl ring with herbicidal, acaricidal and insecticidal activity are described in WO 94/14785, WO 96/02 539, WO 96/35 664, WO 97/01 535, WO 97/02243 , WO 97/02 243, WO 97/36 868, WO 99/05638, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972 and WO 01/74770, WO 03/062244, WO 04 / 080962, DE-A-10326386.
  • W represents alkoxy, haloalkoxy, alkoxy-alkoxy, alkoxy-bisalkoxy, bisalkoxy-alkoxy or optionally substituted cycloalkyl-alkanediyloxy, which can optionally be interrupted by heteroatoms,
  • Y represents alkyl
  • wo ⁇ n for hydrogen each optionally substituted by halogen alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl, in which at least one ring atom is optionally replaced by a heteroatom, or in each case optionally by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy , Cyano or nitro substituted aryl, arylalkyl or hetaryl,
  • B represents hydrogen, alkyl or alkoxyalkyl, or
  • a and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle, optionally containing at least one heteroatom,
  • D represents hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, saturated or unsaturated cycloalkyl, in which optionally one or more ring members are replaced by heteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or
  • a and Ql together represent alkanediyl or alkenediyl optionally substituted by hydroxy, in each case optionally substituted alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl or
  • Q represents hydrogen or alkyl
  • Q ⁇ , Q4, Q5 and Q ⁇ are independently hydrogen or alkyl
  • Q 3 represents hydrogen, optionally substituted alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl (in which a methylene group is optionally replaced by oxygen or sulfur) or optionally substituted phenyl, or
  • Q 3 and Q4 together with the carbon atom to which they are attached represent a saturated or unsaturated, optionally containing a hetero atom, unsubstituted or substituted cycle,
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M represents oxygen or sulfur
  • R2 represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, which is optionally substituted by halogen, or cycloalkyl, phenyl or benzyl which is optionally substituted,
  • R 3 , R4 and R ⁇ independently of one another each represent optionally substituted by halogen substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent optionally substituted phenyl, benzyl, phenoxy or phenylthio, R "and R ⁇ independently represent hydrogen, in each case optionally substituted by halogen, alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, for one optionally substituted by oxygen or Sulfur interrupted cycle.
  • the compounds of the formula (I) can be present in different compositions as geometric and / or optical isomers or isomer mixtures, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and agents containing them are the subject of the present invention. However, for the sake of simplicity, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • A, B, D, G, Q 1 , Q 2 , Q 3 , Q, QA QA W, X and Y have the meaning given above.
  • A, B, D, E, L, M, W, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • A, B, E, L, M, W, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meaning given above. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-3-a) to (I -3-g) if CKE stands for group (3),
  • A, B, E, L, M, W, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meaning given above.
  • the compounds of the formula (1-4) can exist in the two isomeric forms of the formulas (I-4-A) and (I-4-B),
  • the compounds of the formulas (I-4-A) and (I-4-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-4-A) and (I-4-B) can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
  • A, D, E, L, M, W, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • A, E, L, M, W, X, Y, Rl, R 2 , R 3 , R 4 , R ⁇ , R ⁇ and R 7 have the meanings given above.
  • the compounds of the formula (1-6) can exist in the two isomeric forms of the formulas (I-6-A) and (I-6-B),
  • the compounds of the formulas (I-6-A) and (I-6-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-6-A) and (I-6-B) can optionally be separated by physical methods, for example by chromatographic methods.
  • A, B, Q 1 , Q 2 , E, L, M, W, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • the compounds of the formula (1-7) can be present in the two isomeric forms of the formulas (I-7-A) or (I-7-B), which is indicated by the broken line in the Formula (1-7) to be expressed:
  • the compounds of the formulas (I-7-A) and (I-7-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-7-A) and (I-7-B) can optionally be separated by physical methods, for example by chromatographic methods.
  • the compounds of the formula (1-8) can be present in the two isomeric formulas (I-8-A) and (I-8-B),
  • the compounds of the formulas (I-8-A) and (I-8-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formula (I-8-A) and (I-8-B) can optionally be separated in a manner known per se by physical methods, for example by chromatographic methods.
  • A, B, D, W, X and Y have the meanings given above if one
  • A, B, D, W, X and Y have the meanings given above, and
  • R 8 represents alkyl (preferably C i -Co-alkyl), intramolecularly condensed in the presence of a diluent and in the presence of a base.
  • A, B, W, X and Y have the meanings given above, if one
  • A, B, W, X, Y and R ° have the meanings given above, condensed intramolecularly in the presence of a diluent and in the presence of a base.
  • A, B, W, X, Y and R 8 have the meanings given above and
  • V represents hydrogen, halogen, alkyl (preferably Ci-Cg-alkyl) or alkoxy (preferably Ci-Cg-alkoxy), optionally cyclized intramolecularly in the presence of a diluent and in the presence of an acid.
  • A, D, W, X and Y have the meanings given above, if one
  • a and D have the meanings given above, or their silylenol ethers of the formula (Va)
  • W, X and Y have the meanings given above and
  • Hai represents halogen (preferably chlorine or bromine), if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
  • A, B, Ql, Q 2 , W, X and Y have the meaning given above, and
  • R 8 represents alkyl (especially C j -CG alkyl), to intramolecular cyclization, optionally in the presence of a diluent and in the presence of a base.
  • A, B, Q 3 , Q 4 , ⁇ ⁇ W, X and Y have the meaning given above, if
  • A, B, Q 3 , Q 4 , Q 5 , ⁇ A W, X and Y have the meaning given above and
  • R 8 represents alkyl (preferably C 1 -C 6 -alkyl), intramolecularly condensed in the presence of a diluent and in the presence of a base.
  • Hai, X, Y and W have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, or ⁇ ) with compounds of the formula (XI)
  • W, X and Y have the meaning given above, and U represents NH 2 or OR 8 , where R 8 has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of a base, or ⁇ ) compounds of the formula ( XU)
  • A, D, W, X, Y and R 8 have the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of a base.
  • Rl has the meaning given above and Hai stands for halogen (especially chlorine or bromine) or
  • M and R 2 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder and
  • Hai represents halogen (in particular chlorine or bromine), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
  • Me for a mono- or divalent metal preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • t for the number 1 or 2 and R10 ? 11 ? R12 independently of one another represent hydrogen or alkyl (preferably Ci-Cg-alkyl), optionally reacted in the presence of a diluent,
  • R "and L have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
  • W has the meaning given above, optionally in the presence of a diluent, a Cu-I salt (e.g. CuBr, CuJ) and a strong base (e.g. sodium hydride, potassium tert-butoxide).
  • a diluent e.g. CuBr, CuJ
  • a strong base e.g. sodium hydride, potassium tert-butoxide
  • the new compounds of the formula (I) have very good activity as pesticides, preferably as insecticides, acaricides and herbicides.
  • (b 1 ) at least one compound which improves the tolerance of crop plants from the following group of compounds:
  • EP-A-582198 4-carboxy-chroman-4-yl-acetic acid (AC-304415, cf. EP-A-613618), 4-chlorophenoxy-acetic acid, 3,3 '-dimethyl -4-methoxy-benzophenone, l-bromo-4-chloromethylsulfonylbenzene, l- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea (aka N- (2-methoxybenzoyl) - 4 - [(methylamino-carbonyl) amino] benzenesulfonamide), 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethyl-urea, l- [4- (N-4 , 5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea,
  • n a number 0, 1, 2, 3, 4 or 5
  • a 1 represents one of the divalent heterocyclic groupings outlined below,
  • n stands for a number 0, 1, 2, 3, 4 or 5
  • a 2 represents alkanediyl with 1 or 2 carbon atoms optionally substituted by CC 4 alkyl and / or C 1 -C 4 alkoxy-carbonyl and / or CC 4 - alkenyloxy-carbonyl,
  • Rl4 stands for hydroxy, mercapto, amino, -CC 6 alkoxy, -C 6 -alkylthio, -C 6 -Ajkylamino or di- (C] -C -alkyl) -amino,
  • Rl5 for hydroxy, mercapto, amino, -C-C 7 -alkoxy, C C ⁇ -alkenyloxy, C ⁇ -C 6 -alkenyloxy-C ⁇ -C 6 - alkoxy, C ⁇ -C 6 -alkylthio, C ⁇ -C 6 -alkylarnino or di- (C 1 -C 4 -alkyl) amino,
  • Rl 6 represents CC 4 alkyl optionally substituted by fluorine, chlorine and / or bromine,
  • R 7 for hydrogen, each optionally substituted by fluorine, chlorine and / or bromine - -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, -C-C 4 -alkoxy-C C 4 -alkyl, dioxolanyl -C r C 4 - alkyl, furyl, furyl -CC-C -alkyl, thienyl, thiazolyl, piperidinyl, or phenyl which is optionally substituted by fluorine, chlorine and / or bromine or C 1 -C 4 -alkyl,
  • R 8 for hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine, C Ce alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, dC ⁇ alkoxy-C C ⁇ alkyl, dioxolanyl-C C 4 - alkyl, furyl, furyl -CC 4 alkyl, thienyl, thiazolyl, piperidinyl, or phenyl which is optionally substituted by fluorine, chlorine and / or bromine or C 1 -C 4 -alkyl,
  • R 7 and R 18 also together, in each case optionally for CC 4 alkyl, phenyl, furyl, a fused benzene ring or for two substituents, together with the carbon atom to which they are attached, a 5- or 6-membered carboxy cycle form, substituted C 3 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl,
  • Rl9 represents hydrogen, cyano, halogen, or C r C -alkyl, C 3 -C 6 -cycloalkyl or phenyl which are each optionally substituted by fluorine, chlorine and / or bromine,
  • R20 f r is hydrogen, in each case optionally hydroxyl-, cyano-, halogen or C 4 - alkoxy-substituted -C 6 alkyl. C 3 -C 6 cycloalkyl or tri- (CC 4 alkyl) silyl,
  • R 2 represents hydrogen, cyano, halogen, or C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl which is optionally substituted by fluorine, chlorine and / or bromine,
  • X 1 represents nitro, cyano, halo, C ⁇ -C -alkyl, C 4 haloalkyl, -C 4 alkoxy or C 4 - is haloalkoxy,
  • X 2 represents hydrogen, cyano, nitro, halogen, C ⁇ -C 4 -alkyl, C 4 haloalkyl, CC 4 -alkoxy or -C 4 haloalkoxy,
  • X 3 represents hydrogen, cyano, nitro, halogen, CC-alkyl, CC 4 -haloalkyl, C 1 -C 4 -alkoxy or C r C 4 -haloalkoxy,
  • t stands for a number 0, 1, 2, 3, 4 or 5
  • v represents a number 0, 1, 2, 3, 4 or 5
  • R 22 f Is hydrogen or C r C 4 alkyl
  • R23 ⁇ is hydrogen or C r C 4 alkyl
  • R 2 4 for hydrogen, in each case optionally substituted by cyano, halogen or CC alkoxy, C r C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C r C 6 alkylamino or di (C r C-alkyl) - amino, or in each case optionally substituted by cyano, halogen or -CC-substituted C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 -C 6 cycloalkylthio or C 3 -C 6 Cycloalkylamino,
  • R25 represents hydrogen, optionally cyano-, hydroxyl-, halogen or C ⁇ -C 4 -alkoxy-substituted C ⁇ -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 - alkenyl or C 3 -C 6 alkynyl, or C 3 -C 6 cycloalkyl optionally substituted by cyano, halogen or CC 4 alkyl,
  • R 2 ⁇ for hydrogen, optionally substituted by cyano, hydroxy, halogen or CC alkoxy CC 6 alkyl, in each case optionally substituted by cyano or halogen, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl, optionally by cyano, Halogen or C 1 -C 6 -substituted C 3 -C 6 cycloalkyl, or optionally by nitro, cyano, halogen, CC 4 alkyl, C 1 -C 4 haloalkyl, C r C 4 alkoxy or C r C 4 haloalkoxy substituted phenyl, or together with R 2 ⁇ represents C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl optionally substituted by C 1 -C 4 -alkyl,
  • X 4 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, CC 4 -alkyl, CC -haloalkyl, C 1 -C 4 -alkoxy or CC 4 -haloalkoxy
  • X 5 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, CC 4 -alkyl, C 4 haloalkyl, CC 4 -alkoxy or CC is 4 -haloalkoxy.
  • W preferably represents CC 6 -alkoxy, -C-C 6 -haloalkoxy, CC 4 -alkoxy-C 2 -C -alkoxy, Ci-C 4 -alkoxy-bis-C 2 -C 4 -alkoxy or optionally up to three times Fluorine, chlorine, C 1 -C 3 -alkyl or - -alkoxy-substituted C 3 -C 6 -cycloalkyl-C 2 -C 2 -alkanediyloxy, in which a methylene group of the ring can optionally be interrupted by oxygen or sulfur, is preferably halogen, is preferred for CC alkyl,
  • CKE preferably stands for one of the groups
  • A preferably represents hydrogen or in each case optionally substituted by halogen -CC 2 -alkyl, C 3 -C 8 -alkenyl, C 1 -C 10 -alkoxy-C 1 -C 8 -alkyl, al yl, optionally substituted by halogen, Ci-Cö-alkyl or C - [- Cg-alkoxy-substituted C3-Cg-cycloalkyl, in which one or two non-directly adjacent ring members are optionally replaced by oxygen and / or sulfur or for each optionally by Halogen, Ci-Cg-alkyl, C ⁇ -Cg-Halogena-kvl, Cj-Cg-alkoxy, Ci-Cg-haloalkoxy, cyano or nitro substituted phenyl or naphthyl, hetaryl with 5 to 6 ring atoms (for example furanyl, pyridyl , Imidazolyl, triazolyl
  • B preferably represents hydrogen, C 1 -C j 2 -alkyl or C ⁇ -Cg-alkoxy-C -Cg-alkyl or
  • A, B and the carbon atom to which they are attached preferably represent saturated C3-Cio-cycloalkyl or unsaturated C5-C ⁇ o-cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and which, if appropriate, is mono- or disubstituted by Ci-Cg- Alkyl, C3-C ⁇ o-cycloalkyl, Cj-Cg-haloalkyl, C ⁇ -Cg-alkoxy, C j-Cg-alkylthio, halogen or phenyl are substituted or
  • A, B and the carbon atom to which they are attached are preferably C3-Cg-cycloalkyl, which is optionally substituted by Ci-C ⁇ -alkyl by one or two non-directly adjacent oxygen and / or sulfur atoms substituted alkylenediyl, or substituted by an alkylenedioxyl or by an alkylenedithioyl group which, together with the carbon atom to which it is attached, forms a further five- to eight-membered ring or
  • A, B and the carbon atom to which they are attached are preferably C3-Cg-cycloalkyl or C5-Cg-cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached, each optionally by C j -Cg-alkyl, Cj-Cg-alkoxy or halogen-substituted C2-Cg-alkanediyl, C2-Cg-alkenediyl or Cj-Cg-alkanediene-diyl, in which a methylene group is optionally replaced by oxygen or sulfur, D preferably represents hydrogen, in each case optionally substituted by halogen Ci-Ci2-alkyl, C3-Cg-alkenyl, C3-Cg-alkynyl, -C-C ⁇ o-alkoxy-C2-Cg-alkyl, optionally by halogen, -C -C4-alkyl , -C -Q -alk
  • a and Ql together preferably represent in each case optionally single or double, identical or different by halogen, hydroxy, by in each case optionally mono- to triple, identical or different by halogen -CC-alkyl, Ci-Cg-alkoxy, Ci-Cg- Alkylthio, C3-C7-cycloalkyl or benzyloxy or phenyl-substituted C3-Cg-alkanediyl or C4-Cg-alkenediyl, which is optionally substituted once to three times, identically or differently by halogen, Cj-Cg-alkyl or Cj-Cg-alkoxy also one of the groups below, if applicable
  • Q 1 preferably represents hydrogen or C 4 -C 4 alkyl
  • Q 4 , Q- > and Q6 independently of one another preferably represent hydrogen or C j -C4-alkyl
  • Q 3 preferably represents hydrogen, Cj-Cg-alkyl, Cj-Cg-alkoxy-Ci ⁇ -alkyl, C ⁇ Cg- alkylthio-C ⁇ -C2-alkyl, optionally by Ci-C ⁇ alkyl or C [ -C4- Alkoxy substituted C3-Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur or optionally by halogen, C1-C4-AH I, C1-C4-alkoxy, -C-C2-haloalkyl, -C-C2-haloalkoxy, cyano or Nitro substituted phenyl or
  • Q 3 and Q 4 together with the carbon atom to which they are attached, preferably represent a C3-C ⁇ ring which is optionally substituted by C 1 -C 4 -alkyl, C 1 -Q / j-alkoxy or C 1 -C 2 -haloalkyl, in which optionally a ring member is replaced by oxygen or sulfur, preferably represents hydrogen (a) or one of the groups OLR 4 / .R 2 .SOr- R 3 ⁇ R 1 (b), (c), ⁇ 2 (d), / R ( ⁇ ).
  • E represents a metal ion equivalent or an ammonium ion
  • L stands for oxygen or sulfur and M stands for oxygen or sulfur
  • R * preferably represents in each case optionally substituted by halogen C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, poly Ci-Cg-alkoxy-Ci-Cg-alkyl or optionally substituted by halogen, C ⁇ -Cg-alkyl or Cj-Cg-alkoxy C3-Cg-cycloalkyl, in which one or more (preferably not more than two) are not directly Adjacent ring members are replaced by oxygen and / or sulfur, for optionally by halogen, cyano, nitro, Cj-Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkyl, Cj-Cg-haloalkoxy, Ci-Cg-alkylthio or Cj
  • R 2 preferably represents in each case optionally substituted by halogen C [-C20-alkyl, C2-C20-alkenyl, C -Cg-alkoxy-C 2 -Cg-alkyl, poly-C 1 -Cg-alkoxy-C 2 -Cg- alkyl, for C3-Cg-cycloalkyl optionally substituted by halogen, Ci-Cg-alkyl or Ci-Cg-alkoxy or for in each case optionally by halogen, cyano, nitro, Ci-Ci-haloalkyl or Ci-Ci-haloalkoxy substituted phenyl or benzyl,
  • R 3 preferably represents Ci-Cg-alkyl which is optionally substituted by halogen or represents phenyl which is optionally substituted by halogen, Ci-Cg-alkyl, Cj-Cg-alkoxy, Cj-C4-haloalkyl, C ⁇ -C4-haloalkoxy, cyano or nitro or benzyl,
  • R 4 and R5 are preferably independently of one another each optionally substituted by halogen C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylthio, C2 -Cg-alkenylthio, C3-C7-cycloalkylthio or for each optionally by halogen, nitro, cyano, Cj-C4-alkoxy, C ⁇ -C4-haloalkoxy, C1-C4-AUC I- thio, C ⁇ -C4-haloalkylthio, C ⁇ - C4-alkyl or -CC-C4-haloalkyl substituted phenyl, phenoxy or phenylthio,
  • R6 and R 7 independently of one another preferably represent hydrogen, in each case optionally substituted by halogen C 1 -C 6 -alkyl, C3-Cg-cycloalkyl, Cj-Cg-alkoxy, C3 ⁇ C - alkenyl, Cj-Cg-alkoxy-Ci- Cg-alkyl, for phenyl optionally substituted by halogen, Ci-Cg-haloalkyl, Ci-Cg-alkyl or Ci-Cg-alkoxy, optionally substituted by halogen, C -Cg-alkyl, C ⁇ -Cg-haloalkyl or Ci Cg-alkoxy substituted benzyl or together for a C 3 -C 4 -alkylene radical optionally substituted by C 1 -C 4 -alkyl, in which a carbon atom is optionally replaced by oxygen or sulfur,
  • Rl preferably represents hydrogen, in each case optionally substituted by halogen C ⁇ -Cg-alkyl or C ⁇ -Cg-alkoxy, for optionally substituted by halogen, C -C4-alkyl or Cj-C4-alkoxy C3-Cg-cycloalkyl, in which is optionally substituted for a methylene group by oxygen or sulfur, or for phenyl, phenyl, substituted by halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy, C ⁇ -C4-haloalkyl, C ⁇ ⁇ -haloalkoxy, nitro or cyano C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -alkoxy,
  • R * a preferably represents hydrogen or C ⁇ -Cg-alkyl or
  • RI and R ⁇ 4a together preferably represent G4-Cg-alkanediyl
  • R ⁇ 7a and R ⁇ 8a independently of one another preferably represent hydrogen, Oj -Cg-alkyl optionally substituted by halogen or optionally halogen, C ⁇ -Cg-alkyl, Ci-Cg-alkoxy, C ⁇ -C4-haloalkyl, C ⁇ -C4-haloalkoxy, nitro or cyano substituted phenyl or
  • Rl 7a and Rl a together with the carbon atom to which they are attached are preferably a carbonyl group or C5-C7-cycloalkyl optionally substituted by halogen, Ci- ⁇ -allyl or C ⁇ - C4-alkoxy, in which a Methylene group is replaced by oxygen or sulfur,
  • Rl9a un ( j R20a independently of one another preferably represent Ci-C j o-alkyl, C2-Ci Q- alkenyl, Cj-Cio-alkoxy, Ci-Ci Q -alkylamino, C3-C ⁇ o-alkenylamino, di- (C ⁇ -C ⁇ o -alkyl) amino or di- (C3-C ⁇ o-alkenyl) amino.
  • halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • W particularly preferably represents CC -alkoxy, -C-C 4 -haloalkoxy, CC 3 -alkoxy-C 2 -C 3 -alkoxy, - -alkoxy-bis- -qualkoxy or C 3 -C 6 -cycloalkyl-C C 2 - alkanediyloxy, in which a methylene group of the ring can optionally be interrupted by oxygen,
  • X particularly preferably represents chlorine or bromine
  • Y particularly preferably represents methyl, ethyl or propyl
  • CKE particularly preferably stands for one of the groups
  • B particularly preferably represents hydrogen, C 1 -C 4 -alkyl or C 1 -C 2 -alkoxyl-C C 2 -alkyl or
  • A, B and the carbon atom to which they are attached are particularly preferably saturated or unsaturated Cs-Cy-cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and which is optionally monosubstituted or disubstituted by C ⁇ -Cg-alkyl, trifluoromethyl or Cj-Cg-alkoxy, is substituted with the proviso that Q 3 is particularly preferably hydrogen or methyl or
  • A, B and the carbon atom to which they are attached are particularly preferably C5-Cg-cycloalkyl, which is optionally substituted by methyl or ethyl-containing alkylenediyl- or by an alkylenedioxyl by one or two not directly adjacent oxygen or sulfur atoms - or by an alkylenedithiol- A group is substituted which forms a further five- or six-membered ring with the carbon atom to which it is attached, with the proviso that Q 3 particularly preferably represents hydrogen or methyl,
  • A, B and the carbon atom to which they are attached are particularly preferably C3-Cg-cycloalkyl or C5-Cg-cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached, each optionally by Ci - C2-alkyl or C j ⁇ -alkoxy-substituted C2-C4-alkanediyl, C2-C4-alkenediyl or butadienediyl, with the proviso that Q 3 then particularly preferably represents hydrogen or methyl,
  • D particularly preferably represents hydrogen, in each case optionally mono- to trisubstituted by fluorine-substituted C j -Cg-alkyl, C3-Cg-alkenyl, -C-C4-Al oxy-C2-C3 -alkyl, optionally optionally mono- to disubstituted by C1- C4-AHCVI, Cj-C4-alkoxy or C1-C2-haloalkyl-substituted C3-Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen or (but not in the case of the compounds of the formulas (II)) for in each case simply to phenyl or pyridyl substituted twice by fluorine, chlorine, bromine, C1-C4-alkyl, C j -C4-haloalkyl, Cj-C ⁇ -alkoxy or C j -C4-haloalkoxy, or
  • a and D (in the case of the compounds of the formula (I-I)) together with the atoms to which they are bonded represent one of the groups AD-1 to AD-10:
  • a and Ql together are particularly preferably each optionally mono- or disubstituted, identically or differently, by C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy-substituted C3-C4-alkanediyl or
  • Q particularly preferably represents hydrogen
  • Q 2 particularly preferably represents hydrogen
  • Q 4 , Q ⁇ and Q are particularly preferably independently of one another hydrogen or C1-C3-alkyl
  • Q 3 particularly preferably represents hydrogen, C 1 -C 4 -alkyl, or optionally C3-Cg-cycloalkyl which is mono- to disubstituted by methyl or methoxy, or
  • Q 3 and Q 4 particularly preferably together with the carbon to which they are attached, represent a saturated Cf-Cg ring which is optionally substituted by C ] -C2-alkyl or -C-C2-alkoxy and in which a ring member is optionally substituted by oxygen or sulfur is replaced, with the proviso that A then particularly preferably represents hydrogen or methyl, or
  • G particularly preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • Rl particularly preferably represents C 1 -C 6 -alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl or optionally C3 to Cg-cycloalkyl which is monosubstituted or disubstituted by fluorine, chlorine, C 2 -C 12 -alkyl or C 1 -C 2 -alkoxy and in which one or two ring members which are not directly adjacent are replaced by oxygen, optionally by one to two times Fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, -C-C4-alkoxy, C ⁇ -C2-haloalkyl or C ⁇ -C2-haloalkoxy-substituted phen
  • R 2 particularly preferably represents in each case mono- to trisubstituted by fluorine-substituted C 1 -C 6 -alkyl, C2-Cg-alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, optionally optionally by C 1 -C 2 -al yl or C 1 -C 1 -C2-Alkoxy-substituted C3-Cg-cycloalkyl or phenyl or benzyl, each of which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, nitro, -C-C4-alkyl, -C-C3-alkoxy, trifluoromethyl or trifluoromethoxy
  • R 3 particularly preferably represents C 1 -C 6 -alkyl which is optionally monosubstituted to trisubstituted by fluorine or is substituted in each case optionally by
  • R 4 particularly preferably represents Cj-Cg-alkyl, Cj-Cg-alkoxy, Ci-Cg-alkylamino, di- (C j -Cg-alkyl) amino, Cj-Cg-alkylthio, C3-C4-alkenylthio, C3- Cg-Cycloalkylthio or for each optionally simply by fluorine, chlorine, bromine, nitro, cyano, C1-C3-alkoxy, C1-C3 -haloalkoxy, Cj ⁇ -alkylthio, C ⁇ -C3-haloalkylthio, C1-C3-AH VI or trifluoromethyl substituted phenyl, phenoxy or phenylthio,
  • R5 particularly preferably represents CC 6 -alkoxy or -CC 6 alkylthio
  • R 7 particularly preferably represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 1 -C 6 -alkoxy-C] -C 4 -alkyl,
  • R "and R 7 together particularly preferably represent a C 4 -C 5 -alkylene radical optionally substituted by methyl or ethyl, in which a methylene group is optionally replaced by oxygen or sulfur.
  • halogen represents fluorine, chlorine and bromine, in particular fluorine and chlorine.
  • W very particularly preferably represents methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, methoxy-ethoxy, ethoxy-ethoxy, cyclopropyl-methoxy, cyclopentyl-methoxy or cyclohexyl methoxy,
  • X very particularly preferably represents chlorine or bromine
  • Y very particularly preferably represents methyl or ethyl
  • CKE very particularly preferably stands for one of the groups very particularly preferably represents hydrogen, in each case optionally mono- to trisubstituted by fluorine -CC4-alkyl or Cj-C2-alkoxy-Ci-C2-alkyl, for cyclopropyl, cyclopentyl or cyclohexyl and only in the case of the compounds of the formula ( 1-5) for each phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
  • B very particularly preferably represents hydrogen, methyl or ethyl or
  • A, B and the carbon atom to which they are attached very particularly preferably represent saturated C5-Cg-cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and which, if appropriate, is simply replaced by methyl, ethyl, propyl, isopropyl, trifluoromethyl, Methoxy, ethoxy, propoxy or butoxy is substituted, with the proviso that Q 3 very particularly preferably represents hydrogen or
  • A, B and the carbon atom to which they are attached very particularly preferably represent Cg-cycloalkyl, which is formed by two oxygen atoms which are not directly adjacent. holding alkylenedioxyl group, with the proviso that Q 3 very particularly preferably represents hydrogen or
  • A, B and the carbon atom to which they are attached very particularly preferably represent C5-Cg-cycloalkyl or C5-Cg-cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached represent C2-C4-alkanediyl or C2-C4-alkenediyl or butadienediyl, with the proviso that Q 3 then very particularly preferably represents hydrogen,
  • D very particularly preferably represents hydrogen, each optionally mono- to trisubstituted by fluorine -CC4-alkyl, C3-C4-alkenyl, -C-C4-alkoxy-C2-C3-alkyl, for cyclopropyl, cyclopentyl or cyclohexyl or (however not in the case of the compounds of the formulas (II)) for phenyl or pyridyl which is optionally simply substituted by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy or trifluoromethyl,
  • a and D together very particularly preferably represent C3-C5-alkanediyl which is optionally monosubstituted by methyl or methoxy, in which case a carbon atom is replaced by oxygen or sulfur only in the case of CKE (1) or by group AD-1
  • a and Q together very particularly preferably represent C3 ⁇ C4-alkanediyl or optionally mono- or disubstituted by methyl or methoxy
  • Q * very particularly preferably represents hydrogen
  • Q 2 very particularly preferably represents hydrogen
  • Q 4 , Q5 and Q6 very particularly preferably independently of one another represent hydrogen or methyl
  • Q 3 very particularly preferably represents hydrogen, methyl, ethyl or propyl, or
  • Q 3 and Q 4 very particularly preferably, together with the carbon to which they are attached, represent a saturated C5-Cg ring which is optionally simply substituted by methyl or methoxy, with the proviso that A then very particularly preferably represents hydrogen, G very particularly preferably represents hydrogen (a) or one of the groups
  • E stands for an ammonium ion
  • L stands for oxygen or sulfur
  • M oxygen or sulfur
  • R very particularly preferably represents Ci-Cg-alkyl, C2-Cg-alkenyl, C j -C2-alkoxy-C ⁇ -alkyl, C ⁇ -C2-alkylthio-C ⁇ -alkyl or optionally simply substituted by fluorine, chlorine, methyl or methoxy C3-Cg-cyclopropyl or for C 1 -C 4 -alkyl which is monosubstituted by chlorine, for phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 2 very particularly preferably represents in each case mono- to trisubstituted by fluorine-substituted C 1 -C 6 -alkyl, C2-Cg-alkenyl or C 1 -C 4 -alkoxy-C2-C3-alkyl, phenyl or benzyl,
  • R 3 is very particularly preferably represents C j -CG alkyl.
  • W stands for methoxy, ethoxy, n-propoxy, methoxy-ethoxy, cyclopropyl-methoxy
  • A stands for methyl, ethyl, i-propyl, i-butyl or cyclopropyl
  • B stands for hydrogen, methyl or ethyl or
  • A, B and the carbon atom to which they are attached stand out for saturated C 5 -C 6 cycloalkyl, in which a ring atom is optionally replaced by oxygen and which is optionally simply substituted by methyl or methoxy,
  • G stands for hydrogen (a) or for one of the groups
  • E stands for an ammonium ion
  • R 1 stands for C 1 -C 6 -alkyl, C 1 -C 2 -alkoxy-C 1 -alkyl, C 3 -C 6 -cycloalkyl (in particular for cyclopropyl or cyclohexyl), simply substituted by chlorine C 4 -C 4 -alkyl or for optionally simple phenyl substituted by chlorine,
  • R 2 stands for Ci-Cg-alkyl, C3-Cg-alkenyl or benzyl,
  • R 3 stands for C ⁇ -Cg alkyl.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
  • optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
  • herbicide safeners of the formulas (Ha), (üb), (He), (Ild) and (He) which improve crop plant tolerance are defined below.
  • m preferably represents the numbers 0, 1, 2, 3 or 4.
  • a 1 preferably represents one of the divalent heteroeyclic groups outlined below
  • n preferably represents the numbers 0, 1, 2, 3 or 4.
  • a 2 preferably represents methylene or ethylene which is optionally substituted by methyl, ethyl, methoxycarbonyl or ethoxycarbonyl.
  • R * 4 preferably represents hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethyl-a ino or diethylamino.
  • R ⁇ preferably represents hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy, allyloxy, 1-allyloxymethyl-ethoxy, methylthio, ethylthio , n- or i-propylthio, n-, i-, s- or t-butylthio, memylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylarnino, dimethylamino or diethylamino.
  • R ⁇ preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine and / or bromine.
  • R 17 preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, Ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or phenyl substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl ,
  • R * 8 preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl , Ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl Phenyl, or R 17 and R 18 together also represent one of the radicals -CH2-O-CH2-CH2- and -CH2-CH2-O-CH2-, which are optionally substituted by methyl, ethyl
  • R 19 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl, each optionally substituted by fluorine, chlorine and or bromine.
  • R 20 preferably represents hydrogen, optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy methyl, ethyl, n- or i-propyl, n-, i-, s- or t- butyl.
  • R 2 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t- which is optionally substituted by fluorine, chlorine and / or bromine. Butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
  • X 1 preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 2 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 3 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • t preferably represents the numbers 0, 1, 2, 3 or 4.
  • v preferably represents the numbers 0, 1, 2, 3 or 4.
  • R 22 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
  • R 23 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
  • R 24 preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimemylamino or diethylamino, or in each case optionally by cyano, fluorine, chlorine,
  • R 25 preferably represents hydrogen, in each case optionally methyl, ethyl, n- or i-propyl, n-, i- or s-butyl substituted by cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, propenyl, butenyl, propynyl or butynyl, optionally substituted by cyano, fluorine, chlorine or bromine, or cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl.
  • R ⁇ preferably represents hydrogen, each optionally substituted by cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propynyl or butynyl optionally substituted by cyano, fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, or optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoro
  • X 4 preferably represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 5 preferably represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • the compounds of the general formula (Ea) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (cf. WO-A-91/07874, WO-A-95/07897).
  • the compounds of the general formula (Ed) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (cf. DE-A-19621522 / US-A-6235680).
  • the particularly advantageous effect of the particularly and most preferred combination partners from group (b 1 ), in particular with regard to the protection of cereal plants, such as, for example, wheat, barley and rye, but also maize and rice, as crop plants, should be emphasized here.
  • the active compound combinations according to the invention can be used, for example, in the following plants:
  • A, B, D, W, X, Y and R 8 have the meanings given above,
  • acylamino acid esters of the formula (E) are obtained, for example, if amino acid derivatives of the formula (XXIE)
  • W, X and Y have the meanings given above and
  • carboxylic acid activation reagents such as carbonyldiimidazole, carbonyl diimides (such as dicyclohexylcarbondiimide), phosphorylation reagents (such as POCI3, BOP-Cl), halogenating agents e.g. Thionyl chloride, oxalyl chloride, phosgene or chloro-formic acid ester introduced leaving group,
  • A, B, D, W, X and Y have the meanings given above, esterified (Chem. Ind. (London) 1568 (1968)).
  • W, X and Y have the meanings given above and
  • halogenating agents e.g. thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus pentachloride
  • phosphonylation reagents such as (e.g. POCI3, BOP-Cl), carbonyldiimidazole, carbonyldiimides (e.g.
  • dicycloidide table or aromatic hydrocarbons such as toluene or methylene chloride or ethers, for example tetrahydrofuran, dioxane, methyl tert-butyl ether) at temperatures from -20 ° C to 150 ° C, preferably from - 10 ° C to 100 ° C.
  • the substituted cyclic aminocarboxylic acids of the formula (XXVI), in which A and B form a ring, are generally obtainable after the Bucherer-Bergs synthesis or after the Strecker synthesis and are each obtained in different isomer forms.
  • ⁇ the isomers
  • the radicals R and the carboxyl group are in equatorial fashion
  • the isomers in which the amino group and the radicals R are equatorial.
  • A, B, D, W, X, Y. and R ° have the meanings given above,
  • A, B, W, X, Y and R 8 have the meanings given above,
  • A, B and R 8 have the meanings given above and
  • Phenylacetic acids of the formula (XXVE) are also obtained by process (Q).
  • R 8 , X and Y have the meaning given above, and
  • W represents halogen (especially bromine),
  • phenylacetic acid esters of the formula (XXXI-a) are known from application WO 96/35 664 or can be prepared by the processes described there.
  • Phenylacetic acid esters of the formula (XXXI) are also obtained by the process (Q) described below, in which the phenylacetic acids of the formula (XXVE) obtained there are esterified by standard methods.
  • A, B, V, W, X, Y and R 8 have the meanings given above,
  • W, X, Y and R 8 have the meanings given above,
  • benzylthio-carboxylic acid halides of the formula (XXXE) are known and / or can be prepared by known processes (J. Antibiotics (1983), 26, 1589).
  • halogenocarbonylketenes of the formula (VI) required as starting materials in the above processes (D), (E) and (H- ⁇ ) are new. They can be produced by methods known in principle (cf. for example Org. Prep. Proced. Int., 7, (4), 155-158, 1975 and DE-A-1 945 703).
  • W, X and Y have the meanings given above and
  • acid halides such as thionyl chloride, phosphorus (V) chloride, phosphorus (IE) chloride, oxalyl chloride, phosgene or thionyl bromide, if appropriate in the presence of catalysts, such as, for example, diethylformamide, methyl-sterylformamide or triphenylphosphine and, if appropriate, in the presence of bases such as Pyridine or triethylamine.
  • acid halides such as thionyl chloride, phosphorus (V) chloride, phosphorus (IE) chloride, oxalyl chloride, phosgene or thionyl bromide
  • catalysts such as, for example, diethylformamide, methyl-sterylformamide or triphenylphosphine and, if appropriate, in the presence of bases such as Pyridine or triethylamine.
  • the substituted phenylmalonic acids of the formula (XXXEI) are new. They can be produced in a simple manner by known processes (cf., for example, Organikum, VEB German Publishing House of Sciences, Berlin 1977, pp. 517 ff, EP-A-528 156, WO 96/35 664, WO 97/02 243, WO 97/01535, WO 97/36868 and WO 98/05638).
  • U represents OR 8 or NH 2 .
  • R s has the meaning given above
  • A, D and R 8 have the meanings given above,
  • A, B, Q 1 , Q 2 , W, X, Y and R 8 have the meaning given above,
  • the 5-aryl-4-ketocarboxylic acid esters of the formula (VEI) are obtained, for example, if 5-aryl-4-ketocarboxylic acids of the formula (XXXIV)
  • A, B, Ql, Q 2 , W, X and Y have the meaning given above,
  • the 5-aryl-4-ketocarboxylic acids of the formula (XXXIV) are obtained, for example, if 2-phenyl-3-oxo-adipic acid esters of the formula (XXXV)
  • A, B, C, Q 2 , W, X and Y have the meaning given above and
  • R 8 and R 8 are alkyl (in particular C j -Cg alkyl) and
  • R 8 is hydrogen
  • A, B, Ql, Q 2 , W, X, Y, R 8 , R 8 ' have the meaning given above and
  • A, B, Ql, Q 2 and R 8 have the meaning given above and
  • W, X, Y and R 8 have the meaning given above, acylated in the presence of a diluent and in the presence of a base (see, for example, MS Chambers, EJ Thomas, DJ. Williams, J. Chem. Soc. Chem. Commun., (1987), 1228, see also the preparation examples).
  • the compounds of the formulas (XXXVI) and (XXXVE-a) are partly known compounds of organic chemistry and / or can be prepared in a simple manner by methods known in principle.
  • A, B, Q 3 , Q 4 , Q 5 , Q 6 , W, X, Y and R 8 have the meaning given above,
  • 6-aryl-5-ketocarboxylic acid esters of the formula (IX) are obtained, for example, if 6-aryl-5-ketocarboxylic acids of the formula (XXXVIE)
  • A, B, Q 3 , Q 4 , Q 5 , Q 6 , W, X and Y have the meaning given above,
  • A, B, Q 3 , Q 4 , Q 5 , Q 6 , W, X and Y have the meaning given above,
  • A, B, Q 3 , Q 4 , Q 5 , Q 6 , W, X and Y have the meaning given above and
  • R 8 and R 8 are alkyl (preferably C 1 -C 6 -alkyl), and
  • A, B, Q 3 , Q 4 , Q 5 , Q 6 , W, X, Y, R 8 and R 8 ' have the meaning given above,
  • A, B, Q 3 , Q 4 , Q 5 , Q ⁇ and R 8 have the meaning given above,
  • A, D, W, X, Y and R 8 have the meaning given above,
  • acylcarbazates of the formula (XE) are obtained, for example, if carbazates of the formula (XU)
  • the compounds of the formula (XLI) are partly commercially available and partly known compounds or can be prepared by processes known in principle in organic chemistry.
  • oxidizing agents such as NaOCl
  • the 2-alkoxy-substituted 3-phenyl-propenes required for the preparation of the compounds of the formula (XLE) are in principle known compounds in organic chemistry and can be prepared by standard methods by alkylating phenols with allyl halides, followed by a Claisen rearrangement and subsequent Produce alkylation (WO 96/25 395).
  • the acid halides of the formula (XIE), carboxylic anhydrides of the formula (XIV) which are also required as starting materials for carrying out the processes (I), (J), (K), (L), (M), (N) and (O) , Chloroformic acid esters or chloroformic acid thioesters of the formula (XV), chloromothio formic acid esters or chlorodithio formic acid esters of the formula (XVI), sulfonic acid chlorides of the formula (XVE), phosphorus compounds of the formula (XVET) and metal hydroxides, metal alkoxides or amines of the formula (XIX) and (XX) and isocyanates of the Formula (XXI) and carbamic acid chlorides of the formula (XXII) are generally known compounds of organic and inorganic chemistry.
  • Process (A) is characterized in that compounds of the formula (E), in which A, B, D, W, X, Y and R ⁇ have the meanings given above, are subjected to intramolecular condensation in the presence of a base.
  • All inert organic solvents can be used as diluents in process (A) according to the invention.
  • Hydrocarbons such as toluene and xylene, preferably ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone, and alcohols, such as methanol, ethanol, propanol, are preferably usable. Iso-propanol, butanol, iso-butanol and tert-butanol.
  • All conventional proton acceptors can be used as the base (deprotonating agent) when carrying out process (A) according to the invention.
  • Alkali metals such as sodium or potassium can also be used.
  • alkali metal and alkaline earth Metallamides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can be used.
  • reaction temperatures can be varied within a substantial range when carrying out process (A) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
  • Process (A) according to the invention is generally carried out under normal pressure.
  • reaction components of the formula (E) and the deprotonating bases are generally employed in approximately double-equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • Process (B) is characterized in that compounds of the formula (ET) in which A, B, W, X, Y and R 8 have the meanings given above are subjected to intramolecular condensation in the presence of a diluent and in the presence of a base ,
  • All inert organic solvents can be used as diluents in process (B) according to the invention.
  • Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
  • Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol can also be used.
  • All conventional proton acceptors can be used as the base (deprotonating agent) when carrying out process (B) according to the invention.
  • Alkali metals such as sodium or potassium can also be used.
  • Alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
  • the reaction temperatures can be varied within a substantial range when carrying out process (B) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
  • Process (B) according to the invention is generally carried out under normal pressure.
  • reaction components of the formula (EI) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • Process (C) is characterized in that compounds of the formula (IV) in which A, B, V, W, X, Y and R ° have the meaning given above, in the presence of an acid and, if appropriate, in the presence of a diluent intramolecularly cyclized.
  • All inert organic solvents can be used as diluents in process (C) according to the invention.
  • Hydrocarbons such as toluene and xylene, preferably halogenated hydrocarbons, such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, and also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, can preferably be used.
  • Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol can also be used.
  • the acid used can also serve as a diluent.
  • All customary inorganic and organic acids can be used as acid in process (C) according to the invention, e.g. Hydrogen halide acids, sulfuric acid, alkyl, aryl and haloalkyl sulfonic acids, especially halogenated alkyl carboxylic acids such as e.g. Trifluoroacetic acid.
  • reaction temperatures can be varied within a substantial range when carrying out process (C) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
  • Process (C) according to the invention is generally carried out under normal pressure.
  • Process (D) according to the invention is characterized in that carbonyl compounds of the formula (V) or their enol ethers of the formula (Va) are reacted with ketene acid halides of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid acceptor.
  • Halogenated hydrocarbons such as toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene
  • ethers such as dibutyl ether, glycol dimethyl ether, diglycol dimethyl ether and diphenyl ether
  • polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide or N-methyl-pyrrolidone
  • All customary acid acceptors can be used as acid acceptors when carrying out process variant (D) according to the invention.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethyl-aniline can preferably be used.
  • reaction temperatures can be varied within a relatively wide range. It is expedient to work at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C.
  • Process (D) according to the invention is advantageously carried out under normal pressure.
  • Process (E) according to the invention is characterized in that thioamides of the formula (VE) are reacted with ketonic acid halides of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid acceptor.
  • All inert organic solvents can be used as diluents in process variant (E) according to the invention.
  • Hydrocarbons such as toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
  • All customary acid acceptors can be used as acid acceptors when carrying out process (E) according to the invention.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethyl-aniline can preferably be used.
  • reaction temperatures can be varied within a substantial range when carrying out process (E) according to the invention. It is expedient to work at temperatures between 0 ° C. and 250 ° C., preferably between 20 ° C. and 220 ° C.
  • Process (E) according to the invention is advantageously carried out under normal pressure.
  • reaction components of the formulas (VE) and (VI) in which A, W, X and Y have the meanings given above and Hai stands for halogen and optionally the acid acceptors in general are set approximately equimolar amounts.
  • Hai stands for halogen and optionally the acid acceptors in general are set approximately equimolar amounts.
  • the process (F) is characterized in that compounds of the formula (VEI) in which A, B, Q *, Q 2 , W, X, Y and R ° > have the meaning given above, in the presence of a base subject to intramolecular condensation.
  • Diluents which can be used in process (F) according to the invention are all organic solvents which are inert to the reactants.
  • Hydrocarbons such as toluene and xylene, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone are preferably usable.
  • Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol can also be used.
  • All conventional proton acceptors can be used as bases (deprotonating agents) when carrying out process (F) according to the invention.
  • Alkali metal and alkaline earth metal oxides, hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as triethylbenzylammonium chloride, are preferably used.
  • Tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (Cg-Cjo) ammonium chloride) or TDA 1 (tris (methoxyethoxyethyl) amine) can be used.
  • Alkali metals such as sodium or potassium can also be used.
  • Alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
  • reaction temperatures can be varied within a substantial range when carrying out process (F) according to the invention. In general, temperatures between -75 ° C and 250 ° C, preferably between -50 ° C and 150 ° C.
  • the process (F) according to the invention is generally carried out under normal pressure.
  • reaction components of the formula (VI) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • the process (G) is characterized in that compounds of the formula (IX) in which A, B, Q 3 , Q 4 , Q 5 , Q *>, W, X, Y and R ⁇ have the meaning given above , undergoes intramolecular condensation in the presence of bases.
  • All organic solvents which are inert to the reactants can be used as diluents in the process (G) according to the invention.
  • Hydrocarbons such as toluene and xylene, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone are preferably usable.
  • Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol can also be used.
  • Alkali metal and alkaline earth metal oxides, hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, methyl (Adogen 464 ( -C ⁇ o) ammonium chloride) or TDA 1 (tris (methoxyethoxyethyl) amine) can be used.
  • phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, methyl (Adogen 464 ( -C ⁇ o) ammonium chloride) or TDA 1 (tris (methoxyethoxyethyl) amine
  • Alkali metals such as sodium or potassium can also be used.
  • Alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can be used.
  • reaction temperatures can be varied within a relatively wide range when carrying out process (G) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
  • Process (G) according to the invention is generally carried out under normal pressure.
  • reaction components of the formula (IX) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • the process (H- ⁇ ) according to the invention is characterized in that hydrazines of the formula (X) or salts of these compounds are reacted with ketene acid halides of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid acceptor.
  • Chlorinated hydrocarbons such as, for example, mesitylene, chlorobenzene and dichlorobenzene, toluene, xylene
  • further ethers such as dibutyl ether, glycol dimethyl ether, diglycol dimethyl ether and diphenylethane
  • polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide or N-methylpyrrolidone
  • All customary acid acceptors can be used as acid acceptors when carrying out process variant (H- ⁇ ) according to the invention.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethyl-aniline can preferably be used.
  • reaction temperatures can be varied within a relatively wide range. It is expedient to work at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C.
  • the process (H- ⁇ ) according to the invention is expediently carried out under normal pressure.
  • the reaction components of the formulas (VI) and (X), in which A, D, W, X and Y have the meanings indicated above and Hai stands for halogen, and, if appropriate, are used Acid acceptors generally in approximately equimolar amounts.
  • the process (H-ß) is characterized in that hydrazines of the formula (X) or salts of this compound, in which A and D have the meanings given above, with malon esters or malonamides of the formula (XI), in which U , W, X, Y and R 8 have the meaning given above, is subjected to condensation in the presence of a base.
  • Halogenated hydrocarbons such as toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene
  • furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, diphenyl ether, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethyl formamide, can preferably be used and N-methyl-pyrrolidone
  • alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tert-butanol.
  • All conventional proton acceptors can be used as the base (deprotonating agent) when carrying out the process (H- ⁇ ) according to the invention.
  • Alkali metals such as sodium or potassium can also be used.
  • alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethyl-aniline can also be used.
  • reaction temperatures can be varied within a substantial range when carrying out the process (H- ⁇ ) according to the invention. In general, temperatures between 0 ° C and 280 ° C, preferably between 50 ° C and 180 ° C.
  • the process (H- ⁇ ) according to the invention is generally carried out under normal pressure.
  • reaction components of the formulas (XI) and (X) are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 mol).
  • All inert organic solvents can be used as diluents in the process (H- ⁇ ) according to the invention.
  • Hydrocarbons such as toluene and xylene, furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone, and alcohols such as methanol, ethanol, propanol, are preferably usable. Iso-propanol, butanol, iso-butanol and tert-butanol.
  • All conventional proton acceptors can be used as the base (deprotonating agent) when carrying out the process (H- ⁇ ) according to the invention.
  • Alkali metals such as sodium or potassium can also be used.
  • alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
  • reaction temperatures can be varied within a substantial range when carrying out the process (H- ⁇ ) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
  • reaction components of the formula (XE) and the deprotonating bases are generally employed in about twice the molar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • the process (I- ⁇ ) is characterized in that compounds of the formulas (I-l-a) to (I-8-a) are each reacted with carboxylic acid halides of the formula (XIE), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • All solvents which are inert towards the acid halides can be used as diluents in the process (I- ⁇ ) according to the invention.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and also ketones such as acetone and methylisopropyl ketone, furthermore ethers such as diethyl ether, tetrahydrofuran and Dioxane, in addition carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane. If the hydrolysis stability of the acid halide permits, the reaction can also be carried out in the presence of water.
  • Suitable acid binders for the reaction according to the process (I- ⁇ ) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base and N, N-dimethylaniline, and furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, are also preferably usable Alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
  • reaction temperatures in the process according to the invention can be varied within a relatively wide range. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • the starting materials of the formulas (I-l-a) to (I-8-a) and the carboxylic acid halide of the formula (XEI) are generally in each case used in approximately equivalent amounts. However, it is also possible to use the carboxylic acid halide in a larger excess (up to 5 mol). The processing takes place according to usual methods.
  • Process (I- ⁇ ) is characterized in that compounds of the formulas (Ila) to (I-8-a) are reacted with carboxylic anhydrides of the formula (XIV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • the diluents which can be used in the process (I- ⁇ ) according to the invention are preferably those diluents which are also preferred when using acid halides.
  • an excess of carboxylic acid anhydride can also act as a diluent.
  • the acid binders which are optionally added in process (I- ⁇ ) are preferably those acid binders which are also preferred when using acid halides.
  • reaction temperatures can be varied within a substantial range in the process (I- ⁇ ) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • the starting materials of the formulas (I-l-a) to (I-8-a) and the carboxylic anhydride of the formula (XIV) are generally used in approximately equivalent amounts. However, it is also possible to use the carboxylic anhydride in a larger excess (up to 5 mol). The processing takes place according to usual methods.
  • the general procedure is to remove diluent and excess carboxylic acid anhydride and the carboxylic acid formed by distillation or by washing with an organic solvent or with water.
  • Process (J) is characterized in that compounds of the formulas (I-l-a) to (I-8-a) are each reacted with chloroformic acid esters or chloroformic acid thiol esters of formula (XV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Suitable acid binders for the reaction according to process (J) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBA, Hunig base and N, N-dimethylaniline
  • alkaline earth metal oxides such as magnesium and calcium oxide
  • alkali and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate
  • alkali hydroxides such as sodium hydroxide and potassium hydroxide.
  • Diluents which can be used in process (J) according to the invention are all solvents which are inert to the chloroformates or chloroformates.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and are preferably usable
  • Tetralin also halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, hydrogen, chlorobenzene and o-dichlorobenzene, in addition ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, in addition carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane.
  • hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, hydrogen, chlorobenzene and o-dichlorobenzene, in addition ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, in addition carboxylic acid esters
  • reaction temperatures can be varied within a substantial range when carrying out process (J) according to the invention. If one works in the presence of a diluent and an acid binder, the reaction temperatures are generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.
  • the process (J) according to the invention is generally carried out under normal pressure.
  • the starting materials of the formulas (I-l-a) to (I-8-a) and the corresponding chloroformic acid ester or chloroformic acid thiol ester of the formula (XIE) are generally in each case used in approximately equivalent amounts. However, it is also possible to use one or the other component in a larger excess (up to 2 mol).
  • the processing takes place according to usual methods. The general procedure is to remove precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent.
  • Process (K) according to the invention is characterized in that compounds of the formulas (I-l-a) to (I-8-a) are each reacted with compounds of the formula (XVI) in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • chloromothio formic acid ester or chlorodithio formic acid ester of the formula (XVI) is set at 0 to 120 ° C., preferably at 20 to 60 ° C., per mol of starting compound of the formulas (Ila) to (I-8-a) around.
  • Possible diluents added are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides, but also haloalkanes.
  • Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the enolate salt of the compounds (Ila) to (I-8-a) is represented by the addition of strong deprotonating agents such as, for example, sodium hydride or potassium tert-butylate
  • the further addition of acid binders can be dispensed with.
  • acid binders customary inorganic or organic bases are possible, examples being sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
  • the processing takes place according to usual methods.
  • Process (L) according to the invention is characterized in that compounds of the formulas (I-l-a) to (I-8-a) are each reacted with sulfonyl chlorides of the formula (XVE), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Possible diluents added are all inert polar organic solvents such as ethers, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
  • Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
  • the enolate salt of the compounds (I-l-a) to (I-8-a) is represented by the addition of strong deprotonating agents (such as sodium hydride or potassium tert-butylate), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tert-butylate
  • acid binders customary inorganic or organic bases are possible, examples being sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
  • the processing takes place according to usual methods.
  • Process (M) is characterized in that compounds of the formulas (Ila) to (I-8-a) are each reacted with phosphorus compounds of the formula (XVIE), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • phosphorus compounds of the formula (XVIE) if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • 1 mol of compounds (Ila) to (I-8-a) 1 to 2, preferably 1 to 1, 3 moles of the phosphorus compound of formula (XVIE) at temperatures between -40 ° C and 150 ° C, preferably between -10 and 110 ° C.
  • Possible diluents added are all inert, polar organic solvents such as ethers, amides, nitriles, alcohols, sulfides, sulfones, sulfoxides etc.
  • Acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
  • Possible inorganic binders which may be added are conventional inorganic or organic bases, such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to the usual methods of organic chemistry.
  • the end products obtained are preferably purified by crystallization, chromatographic purification or by so-called “distillation", i.e. Removal of volatiles in vacuo.
  • the process (N) is characterized in that compounds of the formulas (Ila) to (I-8-a) are reacted with metal hydroxides or metal alkoxides of the formula (XIX) or amines of the formula (XX), if appropriate in the presence of a diluent ,
  • Diluents which can be used in process (N) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol, but also water.
  • Process (N) according to the invention is generally carried out under normal pressure.
  • the reaction temperatures are generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C.
  • Process (O) is characterized in that compounds of the formulas (Ila) to (I-8-a) are each reacted with (O- ⁇ ) compounds of the formula (XXI), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or (O- ⁇ ) with compounds of the formula (XXE) if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • O- ⁇ about 1 mol of isocyanate of the formula (XXI) is reacted at 0 to 100 ° C., preferably at 20 to 50 ° C., per mole of starting compound of the formulas (Ila) to (I-8-a) ,
  • Possible diluents added are all inert organic solvents, such as ethers, arnides, nitriles, sulfones, sulfoxides.
  • catalysts can be added to accelerate the reaction.
  • Organotin compounds such as e.g. Dibutyltin dilaurate can be used. It is preferably carried out at normal pressure.
  • Possible diluents added are all inert polar organic solvents, such as ethers, arnides, sulfones, sulfoxides or halogenated hydrocarbons.
  • Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the enolate salt of the compound (I-l-a) to (I-8-a) is represented by the addition of strong deprotonating agents (such as sodium hydride or potassium tert-butoxide), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tert-butoxide
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to usual methods.
  • the process (P) is characterized in that compounds of the formulas (Ila 1 ) to (I-8-a ') in which A, B, D, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , X and Y have the meanings given above and W preferably represents bromine, with alcohols of the formula W-OH in which W has the meaning given above in the presence of a base and a Cu-I salt (for example CuBr or CuJ ) implements.
  • All inert organic solvents can be used as diluents in process (P) according to the invention.
  • Hydrocarbons such as toluene and Xylene, also ether, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone, esters such as methyl acetate, ethyl acetate, propyl acetate, and OH alcohols e.g. methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol, tert-butanol, glycol monomethyl ether or diethylene glycol monoethyl ether.
  • ether such as dibutyl ether, tetrahydrofuran, dio
  • All conventional proton acceptors can be used as the base (deprotonating agent) when carrying out process (P) according to the invention.
  • Alkali metals such as sodium or potassium can preferably be used.
  • Alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and preferably also alkali metal alcoholates, such as sodium methylate, sodium ethylate, sodium isopropylate, sodium tert-butoxide and potassium tert-butoxide, can also be used.
  • reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
  • the process (P) according to the invention is generally carried out under normal pressure.
  • reaction components of the formulas (II-a ') to (I-8-a') are generally employed in excess of the alcohols W-OH and the bases up to 20 mol, preferably 3 to 5 moles around.
  • the copper I salts are generally used catalytically: 0.001 to 0.5 mol, preferably 0.01 to 0.2 mol. However, it is also possible to use them in equimolar amounts.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura for example Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Homoptera
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomoriurn pharaonis, Vespa spp.
  • Plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • the compounds or active compound combinations according to the invention can, if appropriate, also be used as herbicides in certain concentrations or application rates. If appropriate, the compounds can also be used as intermediates or precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants that are cultivated by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or by com- Binations of these methods can be obtained, including the transgenic plants and including plant varieties that can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include Erategut and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and plant parts according to the invention with the active substances or combinations of active substances takes place directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the active substances or combinations of active substances can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and Fine encapsulation in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ammonium salts and natural rock meals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates, come as solid carriers for granules
  • suitable emulsifying and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to spread the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Ampropylfos Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin;
  • bilanafos binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate; Buthiobate;
  • cyprodinil cyprofuram
  • Dagger G debacarb
  • dichlofluanid dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol;
  • dimethomorph dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines;
  • Flubenzimine Flubenzimine; fludioxonil; flumetover; Flumo ⁇ h; fluoromides; fluoxastrobin; fluquinconazole;
  • flurprimidol flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium;
  • fuberidazole furalaxyl; furametpyr; Furcarbanil; Furmecyclox; guazatine; Hexachlorobenzene;
  • isoprothiolane Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone;
  • mepanipyrim mepronil; metalaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam;
  • metiram metiram
  • metominostrobin Metsulfovax
  • Müdiomycin Metominostrobin
  • myclobutanil Metozoline
  • natamycin metiram
  • nicobifen Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefurazoate; penconazole;
  • pencycuron phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole;
  • prochloraz procymidone; propamocarb; Propanosine-sodium; propiconazole; propineb; Proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon;
  • Thicyofen Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid;
  • trifloxystrobin triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin;
  • DDT Deltamethrin, Demeton-S-methyl, Demeton-S-methylsulphone, Diafenthiuron, Dialifos, Diazinone, Dichlofenthion, Dichlorvos, Dicofol, Dicrotophos, Dicyclanil, Diflubenzuron, Dimefluthrin, Dimethoate, Dinobutyl, Dinobutinophone, Dimobutinophone Disulfoton, Docusat-sodium, Dofenapyn, DOWCO-439,
  • Famphur Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fensulfo- thione, fenthion, Fentrifanil, fenvalerate, fipronil, flonicamid, fluacrypyrim, fluazuron, Flubenz- imine, Flubrocythrinate, flucycloxuron, Flucythrinate, flufenerim, flufenoxuron, flufenprox, Flu- methrin, Flupyrazofos, Flutenzin (Flufenzine), fluvalinate, fonofos, Formetanate, formothion , Fosmethilan, Fosthiazate, Fubfenprox (F
  • Halofenozide HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydra-methylnone, Hydroprene,
  • Mecarbam Mesulfenfos, Metaldehyde, Metam-sodium, Methacrifos, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metofluthrin, Metolcarb, MilevinphinineMoxinphinineMoxinphinine, Metoxinphinine, Metoxinphine, Moxinphin, Miloxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxinphin, Moxin 245, MON-45700, Monocrotophos, Moxidectin, MTI-800,
  • NC-104 NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron,
  • Paecilomyces fumosoroseus Parathion-methyl, Parathion (-ethyl), Permethrin (eis, trans-), Petroleum, PH-6045, Phenothrin (lR-trans isomer), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Piperonyl butoxide, Pirimicarb, Pirimiphos-methyl, Pirimiphos-ethyl, Potassium oleate, Prallethrin, Profenofos, Profluthrin, Promecarb, Propaphos, Propargite, Propetamphos, Propoxur, Prothiofos, Prothoate, Protrifenbute, Pymetclhrosine, Pymetclhrosine, Pymetrohrosine Pyridaben, Pyridalyl, Pyridaphenthion, Pyridathion, Pyrimidifen, Pyrip
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself being active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient or combination of active ingredients When used against hygiene pests and pests of stored products, the active ingredient or combination of active ingredients is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • all plants and their parts can be treated.
  • wildly occurring or by conventional tional biological breeding methods such as crossing or protoplast fusion, plant species and plant varieties obtained and their parts treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant cultivars which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvest products, higher shelf life and / or workability of the harvest products possible, which go beyond the effects to be expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the crop products , higher shelf life and / or workability of the harvested products.
  • Such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed, Beets, sugar cane and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby corn, soybeans, potatoes, cotton and rapeseed are particularly emphasized.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryEA, CryEIA, CryIEB2, Cry9c, Cry2Ab, Cry3Bb and CryJ-F and their combinations) are generated in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Examples of “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YTELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), MI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties marketed under the name Clearf ⁇ eld® (eg maize). It goes without saying that these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously with the compounds according to the invention or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active substances or combinations of active substances according to the invention not only counteract
  • animal parasites ectoparasites
  • tick ticks leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Pht ⁇ rus spp., Solenopotes spp ..
  • Nematocerina and Brachycerina e.g. Aedes s -.pp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp.
  • Haematopota spp. Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • active substances or combinations of active substances according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats,
  • the fight against these arthropods is intended to reduce deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.), so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
  • the active substances or combinations of active substances according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as for example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on) , washing, pumping in and with the help of active substance-containing shaped bodies such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • the active ingredients or combinations of active ingredients can be formulated (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Uroceras augur.
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected from insect infestation is very particularly preferably wood and wood processing products.

Abstract

L'invention concerne de nouveaux cétoénols cycliques 2,4,6-phénylsusbtitués de formule (I), dans laquelle CKE, W, X et Y ont les significations spécifiées dans la description, plusieurs procédés et produits intermédiaires pour leur fabrication, leur utilisation comme pesticides et/ou comme herbicides, ainsi que des agents herbicides sélectifs renfermant, d'une part, les cétoénols cycliques 2,4,6- phénylsubstitués et, d'autre part, un composé améliorant la compatibilité avec les plantes cultivées.
PCT/EP2005/002605 2004-03-25 2005-03-11 Cetoenols cycliques 2,4,6-phenylsubstitues WO2005092897A2 (fr)

Priority Applications (13)

Application Number Priority Date Filing Date Title
AT05728341T ATE556078T1 (de) 2004-03-25 2005-03-11 2,4,6-phenylsubstituierte cyclische ketoenole
US10/594,251 US7947704B2 (en) 2004-03-25 2005-03-11 2,4,6-phenyl-substituted cyclic ketoenols
KR1020067021888A KR101137808B1 (ko) 2004-03-25 2005-03-11 2,4,6-페닐 치환된 사이클릭 케토에놀
CA002561076A CA2561076A1 (fr) 2004-03-25 2005-03-11 Cetoenols cycliques 2,4,6-phenylsubstitues
EP05728341A EP1732930B1 (fr) 2004-03-25 2005-03-11 Cetoenols cycliques 2,4,6-phenylsubstitues
AU2005225508A AU2005225508A1 (en) 2004-03-25 2005-03-11 2,4,6-phenylsubstituted cyclic ketoenoles
MXPA06010781A MXPA06010781A (es) 2004-03-25 2005-03-11 Cetoenoles ciclicos 2,4,6-fenilsubstituidos.
BRPI0507876A BRPI0507876B1 (pt) 2004-03-25 2005-03-11 cetonóis cíclicos 2,4,6-fenil substituídos, seu processo de produção, seus usos e seus intermediários, defensivos e/ou herbicidas e seu processo de produção, processos para controle de pragas animais e/ou crescimento de plantas indesejáveis, agente e seu uso
ES05728341T ES2384175T3 (es) 2004-03-25 2005-03-11 Cetoenoles cíclicos 2,4,6-fenil-sustituidos
JP2007504296A JP5004788B2 (ja) 2004-03-25 2005-03-11 ２，４，６−フェニル置換環状ケトエノール
UAA200611221A UA85872C2 (uk) 2004-03-25 2005-11-03 2,4,6-фенілзаміщені циклічні кетоеноли та засіб для боротьби з шкідниками або бур'янами
US13/087,696 US20110195842A1 (en) 2004-03-25 2011-04-15 2,4,6-Phenyl-Substituted Cyclic Ketoenols
US13/087,879 US20110213160A1 (en) 2004-03-25 2011-04-15 2,4,6-Phenyl-Substituted Derivatives

Applications Claiming Priority (2)

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DE102004014620A DE102004014620A1 (de) 2004-03-25 2004-03-25 2,4,6-phenylsubstituierte cyclische Ketoenole
DE102004014620.9 2004-03-25

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US13/087,879 Division US20110213160A1 (en) 2004-03-25 2011-04-15 2,4,6-Phenyl-Substituted Derivatives
US13/087,696 Division US20110195842A1 (en) 2004-03-25 2011-04-15 2,4,6-Phenyl-Substituted Cyclic Ketoenols

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ES2384175T3 (es) 2012-07-02
US20110195842A1 (en) 2011-08-11
EP1732930B1 (fr) 2012-05-02
ZA200607869B (en) 2008-04-30
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ATE556078T1 (de) 2012-05-15
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RU2384570C2 (ru) 2010-03-20
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UA85872C2 (uk) 2009-03-10
US20070298968A1 (en) 2007-12-27
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EP1732930A2 (fr) 2006-12-20
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BRPI0507876B1 (pt) 2015-10-13
BRPI0507876A (pt) 2007-07-24
AU2005225508A1 (en) 2005-10-06
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